1. Field of the Invention
The present invention relates to a process for producing azine compounds and oxime compounds that are useful as intermediate materials for polyamides or as intermediates in the organic synthesis.
2. Description of the Related Art
Oxime compounds have been conventionally produced by, for example, a process of subjecting a carbonyl compound and hydroxylamine to dehydration condensation, a process of catalytically hydrogenating a nitroalkenone in the presence of a palladium catalyst, or a process of subjecting a hydroxyaminoalkane to air oxidation in the presence of a divalent cobalt. However, these processes require relatively expensive material compounds.
Cyclohexanone oxime is commercially produced by a process in which cyclohexane is irradiated with radiation in the presence of nitrosyl chloride to thereby yield cyclohexanone oxime via nitrosocyclohexane. This process can directly convert cyclohexane into cyclohexanone oxime and can thereby reduce production costs. However, nitrosyl chloride used as a raw material is generally prepared by a reaction between nitrogen monoxide and chlorine, thus invites complicated facilities and decreased operability and imposes heavy loads on the environment.